Always Judging's Courtney Trop Just Did the Sickest Photo Shoot in Rare Vintage

Courtney Trop, the style wunderkind behind fashion blog Always Judging, feels like she wears more vintage than any other influencer. "I'm a Pisces, which is the oldest sign, so it's fitting that I'd want to wear old clothes," she says. "I feel like I've lived other lives."

A few weeks before Trop's 32nd birthday, she hit up team Who What Wear with a set of exclusive photos to share. This was a special shoot—hair, makeup, styling, and photography were all executed by a team of Trop's close personal friends. In the images, Trop is wearing rare secondhand designer threads from What Goes Around Comes Around (WGACA), a high-end boutique full of hard-to-find vintage with several locations around the country, including Beverly Hills, near where Trop resides.

Opportunities to shoot with fashion brands obviously come Trop's way all the time, but even a brief scroll through her Instagram feed will reveal that the influencer, who is currently rocking a lion-like perm and is often pictured in almost-freaky vintage couture (head-to-toe cornflower leather, shoulder pads, magenta silk—"Everything I wear has a story behind it," Trop says. "Vintage excites me more than new clothes"), has a strong point of view, and she turns most offers down. This photo shoot only came together after a long process of courting. "WGACA had reached out to me before, and I never wanted to work with them because I thought they were overpriced and I already had my vintage contacts," says Trop. But after revisiting the opportunity, Trop changed her mind. "I realized their pieces are really rare and amazing and curated and special."

Trop and her friends had never gotten booked all together on a shoot before, so they thought Why not? Here's the perfect chance; let's do it. She and her stylist friend Joni pulled a bunch of looks from WGACA, and they all met in Trop's backyard to play for a few hours. "I think it's really special that we all wanted to work on a Sunday for no money," says Trop. Keep scrolling to see how the looks and photos turned out and to learn more about the clothes.

Photo:

Drew Escriva

Photo:

Drew Escriva

Photo:

Drew Escriva

The look above was what Trop says was the most fun to wear: a vintage Jean-Paul Gaultier top and Dior dress paired with new Collina Strada gloves, Maryam Nassir Zadeh shoes, and a beaded crown made by the stylist herself.

"Joni makes all these headpieces out of beads," Trop told us. "Most stylists come to a shoot with nothing but pins and tape, but she comes with all these cool accessories."

Photo:

Drew Escriva; Clothes: vintage Dior top, Dior jacket, Dior skirt

Photo:

Drew Escriva

In terms of concept, from hair to makeup to styling to photography, the team wanted to create an interesting juxtaposition of hard and soft. "Joni took into consideration that I have this punk side to me, so she mixed a lot of hard and soft looks, layering vintage Dior over something a little harder, and there are elements of that in the photos too," says Trop. 

Drew, her photographer, explains the direction this way: "As an intimate friend of Courtney's, I wanted to see her jump into a character and transform. Style is such an important part of identity, and even more so for Courtney, so I wanted our shoot to excite her and push her boundaries. I wanted to see her play in the ethereal and in the morose, simultaneously."

Photo:

Drew Escriva

Photo:

Drew Escriva

Photo:

Drew Escriva

Trop's favorite look of this day was this vintage Versace jacket, Jean-Paul Gaultier tee, and Jean-Paul Gaultier pants paired with new Helmut Lang boots and a stylist-made beaded wallet. "The JPG 'safe sex' shirt is really hard to find," says Trop. "I never knew WGACA had such special vintage."

Photo:

Drew Escriva

Photo:

Drew Escriva

Photo:

Drew Escriva

Photographer: Drew Escriva; Stylist: Joanie Del Santo; Makeup: Matisse Andrews; Hair: Jefferson T 

Next: Don't miss 23 of the coolest places to buy vintage clothing online.